Hydrochloric Acid → Ammonium Hydroxide

HRID 1615846Notes

Reaction equation

HRID 1615846 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8](OC)=[O:9])=[C:4]([C:12](OC)=[O:13])[CH:3]=1.[BH4-].[Na+].CO.Cl>C1COCC1.O>[NH4+:7].[OH-:9].[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([CH2:12][OH:13])[CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 12243913dimethyl 6-chloropyridine-3,4-dicarboxylate

Product 2

HCID 14923Ammonium HydroxideHCID 57753231HCID 57753231, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of dimethyl 6-chloropyridine-3,4-dicarboxylate from Step B (1.26 g, 5.50 mmol) in THF (10 mL) at 0° C. was added sodium borohydride (1.07 g, 28.2 mmol) carefully. To the resulting mixture was added MeOH (5 mL), dropwise, over 20 min. The reaction mixture was stirred at 0° C. for 1 h, then H2O (5 mL) and 1 N HCl (5 mL) were added and the mixture was concentrated to dryness in vacuo. The residue was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH:NH4OH—100:0:0 to 80:20:0.2, to give the title compound. MS: m/z=174 (M+1).

Workup

  1. concentrationthe mixture was concentrated to dryness in vacuo
  2. customThe residue was purified by silica gel chromatography
  3. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-4027193ed53d41459a04e8fc56601c6a
Source dataset
uspto-grants-2014_07
Patent number
US08765759B2

Reaction notes

Loading…